EP0915817B1 - Verfahren zur herstellung von kristallinem d-sorbit - Google Patents

Verfahren zur herstellung von kristallinem d-sorbit Download PDF

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Publication number
EP0915817B1
EP0915817B1 EP97935531A EP97935531A EP0915817B1 EP 0915817 B1 EP0915817 B1 EP 0915817B1 EP 97935531 A EP97935531 A EP 97935531A EP 97935531 A EP97935531 A EP 97935531A EP 0915817 B1 EP0915817 B1 EP 0915817B1
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EP
European Patent Office
Prior art keywords
sorbitol
melt
temperature
crystalline
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Revoked
Application number
EP97935531A
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German (de)
English (en)
French (fr)
Other versions
EP0915817A1 (de
Inventor
Pedro Gutmann
Jakob Wiesenbart
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MG Technologies AG
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MG Technologies AG
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Application filed by MG Technologies AG filed Critical MG Technologies AG
Publication of EP0915817A1 publication Critical patent/EP0915817A1/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/78—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by condensation or crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/26—Hexahydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Definitions

  • the invention relates to a method for producing crystalline D-sorbitol by evaporation of an aqueous D-sorbitol solution in vacuum and subsequent Melt crystallization of those obtained by evaporation D-sorbitol melt.
  • D-sorbitol belongs to the 6-valent alcohols and has the empirical formula C 6 H 14 O 6 .
  • D-sorbitol is made from D-glucose by electrolytic reduction or catalytic hydrogenation.
  • D-sorbitol has a sweet taste and is used as a sugar substitute and in the cosmetic and pharmaceutical industries as well as for the production of polyethers and surfactants.
  • D-sorbitol crystallizes in the ⁇ , ⁇ and ⁇ modification, the ⁇ modification being the thermodynamically stable form.
  • D-sorbitol is used either in the form of concentrated aqueous solutions or in solid crystalline form as an industrial raw material. In order to be able to handle the solid crystalline D-sorbitol well, the aim is that it is present as far as possible in the ⁇ modification, since this form is not only thermodynamically stable but also comparatively less hygroscopic.
  • DE-A 32 45 170 describes a process for the production of Known sorbitol with improved tableting properties, where a solution of crystallized glucose in a Hydrogenated below 170 ° C and the resultant Sorbitol solution at a temperature of 140 to 170 ° C so is spray dried that the product obtained a Has water content of less than 1%.
  • DE-C 23 50 619 describes a process for continuous Production of crystallized sorbitol by introducing melted and granular sorbitol in a container in which the mass thus obtained at an elevated temperature in Movement is known.
  • the circulated mass is on a Temperature kept above 90 ° C and which is mainly on the surface of the circulating mass secreting larger Grains are rotating by overflowing at the exit
  • the Melt crystallization is a vessel for vacuum evaporation upstream, which is suitable for a sorbitol solution bring a dry content of over 98% by weight.
  • EP-A 0032288 contains a modified ⁇ -sorbitol advantageous tableting properties known, the one Has a melting point of 100 to 101 ° C and a crystalline Share> 90%.
  • This product is manufactured by Melt crystallization in a mixing device, which is the melt is fed at 96 to 97 ° C, in which the melt is kneaded and is cooled and a hot air flow to prevent a premature crystallization is supplied.
  • EP-A 0330352 discloses a process for the production of solid Sorbitol, in the case of seed crystals in a sorbitol melt by stirring be dispersed and at which the temperature of the sorbitol melt is set so that the melt does not solidify and that the Do not melt seed crystals. Then the with Seed crystals offset melt for at least a time Cooled for 5 minutes to a temperature of 50 to 85 ° C, whereby forms a solid which is then cooled to room temperature.
  • the sorbitol seed crystals can be fats, oils and / or Surface-active substances contain and become the sorbitol melt added in an amount of 1 to 50% by weight.
  • a concentrated sorbitol solution is applied to a process mechanically agitated bed dripped from crystallized sorbitol or roughly sprayed.
  • the moving and wetted crystal bed becomes the evaporation of the water while passing air or inert gas at a temperature of 60 to 80 ° C.
  • After an appropriate crystallization time is under Part of the solid sorbitol is continuously cooled taken.
  • the product thus obtained also has a very wide grain spectrum.
  • Another disadvantage is that the individual sorbitol particles with low moisture absorption quickly baked into hard masses from the air and that the Dissolving time in water is relatively high.
  • the invention has for its object a method for Production of crystalline D-sorbitol to create that after works on the principle of melt crystallization, but that avoids known disadvantages of melt crystallization.
  • the crystalline D-sorbitol produced according to the invention a melting point of 98 to 100 ° C, a water content ⁇ 0.5 % By weight and a content of ⁇ modification> 90%.
  • On such product has optimal usage properties its use as an industrial raw material. So that's it Manufacturing process based on the principle of Melt crystallization with upstream vacuum evaporation works to educate or improve so that the Product quality requirements safely and via one longer operating periods are reliably observed, an economical way of working is also required is.
  • a D-sorbitol melt with a water content ⁇ 0.5 wt% and a temperature that is 5 to 15 ° C above the Solidification point of the melt lies in one Melt crystallizer is crystallized from a cooled container and a horizontally arranged, rotatable, equipped with disc elements and mixed bars Wave exists, the disc elements and / or mixed bars in Form of a snail are arranged on the shaft and in which the disc elements, the mixed bars and / or the shaft be cooled and that the the melt crystallizer removed crystals by grinding and sieving into one End product are processed that are> 90% crystalline D-sorbitol of the ⁇ modification exists.
  • the melt crystallization according to the invention eliminates the Need to add solid D-sorbitol to the D-sorbitol melt, because of the design according to the invention the melt crystallization becomes nuclei in sufficient amount formed. Due to the relatively high mechanical energy input, which by the invention Mixing organs using, crystals are with produced small average particle size in which only one very small amount of melt is included, so that End product not noticeably contaminated by amorphous D-sorbitol is. In the method according to the invention, therefore advantageously on a ripening of the product, that is the conversion of amorphous or in the ⁇ and ⁇ modification D-sorbitol present in the ⁇ modification, waived become.
  • melt crystallization according to the invention brings about further advantageously that the effort for grinding can be kept low.
  • Melt crystallizer a very favorable course of the Melt crystallization reached, which leads to that End product has a ⁇ modification content> 90%, whereby the maturation of the product can be omitted.
  • an aqueous solution with a D-sorbitol content from 60 to 80% by weight by evaporation at 5 to 200 mbar, preferably 50 to 200 mbar, and 130 to 170 ° C, preferably 130 to 140 ° C, in a D-sorbitol melt with a Water content ⁇ 0.5% by weight is transferred and if the D-sorbitol melt is cooled to a temperature 5 to 15 ° C, preferably 10 to 15 ° C, above the Solidification point of the melt.
  • the D-sorbitol melt is cooled to a temperature of 105 to 115 ° C, that the D-sorbitol melt in the melt crystallizer has an average residence time of 1 to 5 hours and that the melt crystallizer removed crystals have an average particle diameter d 50 of ⁇ 2 mm. Under these process conditions, a high quality end product can be produced safely.
  • aqueous one in a storage tank (1) D-sorbitol solution with a D-sorbitol content of approx. 70% by weight.
  • D-sorbitol is through Catalytic hydrogenation of D-glucose in aqueous solution manufactured. After the production of D-sorbitol, the cleaned aqueous solution and up to a D-sorbitol content of approx. 70% by weight.
  • the storage tank (1) is with provided a stirrer, not shown in the drawing.
  • the aqueous D-sorbitol solution passes through line (2) continuously in the thin film evaporator (3), which is equipped with a Stirrer (4) is equipped, which one or more Wiper blades (5) carries.
  • the aqueous D-sorbitol solution trickles in a thin film on the wall of the thin film evaporator (3) and is heated to a temperature of approx. 135 ° C heated by the heating medium in the heating jacket (6).
  • the Thin film evaporator (3) is the aqueous D-sorbitol solution the water is withdrawn to a residual content of ⁇ 0.5% by weight.
  • the Evaporation of the water takes place at about 100 mbar, and the Water vapor is removed from the thin film evaporator (3) Line (7) discharged.
  • the in the thin film evaporator (3) generated D-sorbitol melt is from the wall of the Thin film evaporator (3) through the wiper blades (5) continuously removed and flowing from the lower part of the Thin film evaporator (3) continuously via line (8) with a temperature of about 135 ° C in the cooler (9), where it is cooled to a temperature of about 110 to 115 ° C.
  • the D-sorbitol melt has good under these conditions Flow properties so that continuous operation is not is disabled.
  • the flowing in the line (8) D-sorbitol melt is brought to normal pressure so that the Cooler (9) works at normal pressure.
  • the cooled D-sorbitol melt is fed via line (10) with a temperature of 110 to 115 ° C continuously in the Melt crystallizer (11) introduced.
  • the Melt crystallizer (11) is a cylindrical container executed, and he has a cooling jacket (12) over which heat is dissipated by a cooling medium.
  • the Melt crystallizer (11) with a rotatable shaft (13) equipped on the disc elements (14) and mixed bars (15) are arranged. Both the shaft (13) and the Disc elements (14) and the mixing bars (15) are from flows through a cooling medium, so that this too Apparatus parts heat from the melt crystallizer (11) is dissipated.
  • the mixed bars (15) are on the Disc elements (14) arranged helically, so that the radial caused by the disc elements (14) Mixing effect caused by one of the mixing bars (15) axial transport effect is superimposed. Also done through the disc elements (14) and the mixing bars (15) one Comminution of those formed in the melt crystallizer (11) Crystal agglomerates. In the front zone of the Melt crystallizer (11) passes the D-sorbitol melt into one plasticine mass over. In the middle zone of the Melting crystallizer (11) is cooled further and already solidified D-sorbitol mass by the over the Mixing elements caused mechanical energy input broken up.
  • the broken mass is further crushed, and it there is also an internal circulation of part of the formed crystalline D-sorbits in the middle and front Zone of the melt crystallizer (11).
  • the powdery crystalline D-sorbitol is arranged on a side Discharged from the melt crystallizer (11) in which a height-adjustable weir is arranged over which the amount of D-sorbitol in the melt crystallizer (11) can be regulated.
  • the crystalline D-sorbitol leaves the Melt crystallizer (11) with a temperature of 40 to 60 ° C.
  • the mixed bars (15) in particular are for this responsible that it is not in the melt crystallizer (11) Caking comes.
  • the crystalline D-sorbitol reaches the mill (17) via line (16), where the product is ground.
  • the grinding work is relatively small since the crystalline D-sorbitol always leaves the melt crystallizer (11) with an average particle diameter d 50 of ⁇ 2 mm, but generally with an average particle diameter d 50 of ⁇ 1 mm.
  • the ground product is fed via line (18) to a sieve (19), from which the end product with the required grain spectrum is removed via line (20).
  • the oversize fraction is returned to the mill (17) via line (21), while the undersize fraction passes through line (22) to the storage tank (1), where it is stirred in the aqueous D-sorbitol solution is dissolved.
  • the end product discharged via line (20) has one Melting point of approx. 98 to 100 ° C, a water content of ⁇ 0.5% by weight and a proportion of ⁇ modification> 90%, where in generally the proportion of the ⁇ modification is approximately 95%.
  • crystalline D-sorbitol has good usage properties because it has good flowability, and in its storage the individual crystals do not stick together.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Saccharide Compounds (AREA)
  • Glass Compositions (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
  • Noodles (AREA)
EP97935531A 1996-07-23 1997-07-21 Verfahren zur herstellung von kristallinem d-sorbit Revoked EP0915817B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19629640 1996-07-23
DE19629640A DE19629640C1 (de) 1996-07-23 1996-07-23 Verfahren zur Herstellung von kristallinem D-Sorbit
PCT/EP1997/003924 WO1998003457A1 (de) 1996-07-23 1997-07-21 Verfahren zur herstellung von kristallinem d-sorbit

Publications (2)

Publication Number Publication Date
EP0915817A1 EP0915817A1 (de) 1999-05-19
EP0915817B1 true EP0915817B1 (de) 2001-06-13

Family

ID=7800564

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97935531A Revoked EP0915817B1 (de) 1996-07-23 1997-07-21 Verfahren zur herstellung von kristallinem d-sorbit

Country Status (14)

Country Link
US (1) US6150570A (pt)
EP (1) EP0915817B1 (pt)
JP (1) JP2001505186A (pt)
KR (1) KR100584828B1 (pt)
CN (1) CN1087727C (pt)
AT (1) ATE202068T1 (pt)
DE (2) DE19629640C1 (pt)
DK (1) DK0915817T3 (pt)
ES (1) ES2159872T3 (pt)
GR (1) GR3036335T3 (pt)
IN (1) IN182140B (pt)
PT (1) PT915817E (pt)
TW (1) TW474942B (pt)
WO (1) WO1998003457A1 (pt)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7266832B2 (en) * 2001-06-14 2007-09-04 Digeo, Inc. Advertisement swapping using an aggregator for an interactive television system
EP1694278A4 (en) 2003-12-16 2009-08-12 Ipsen Pharma GLP-1 PHARMACEUTICAL COMPOSITIONS
WO2005123640A1 (en) * 2004-06-17 2005-12-29 Cargill, Incorporated Steam agglomeration of polyols
US7776125B2 (en) * 2006-05-31 2010-08-17 Oms Investments, Inc. Composition and method for inhibiting caking in a urea containing fertilizer
JP2010181087A (ja) * 2009-02-05 2010-08-19 Kurimoto Ltd 潜熱蓄熱材の排出方法
CN102249857B (zh) * 2011-06-10 2013-06-19 天津大学 一种d-山梨醇的结晶固体及其制备方法
EP3784640A1 (en) 2018-04-25 2021-03-03 OMS Investments, Inc. Fertilizer compositions having slow-release nitrogen compounds and methods of forming thereof
CN109942375B (zh) * 2019-04-25 2022-03-04 浙江华康药业股份有限公司 一种防止液体山梨糖醇结晶的方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD76487A (pt) *
DD49322A (pt) *
US1724627A (en) * 1927-03-21 1929-08-13 Bernard H Varnau Sugar-crystallizing apparatus
US2315699A (en) * 1939-07-27 1943-04-06 Atlas Powder Co Crystallization of sorbitol
US2594863A (en) * 1948-12-24 1952-04-29 Atlas Powder Co Crystallization of sorbitol
US3330874A (en) * 1963-01-31 1967-07-11 Pfizer & Co C Sorbitol crystallization process
FR2202867B1 (pt) * 1972-10-13 1978-02-10 Roquette Freres
US4293570A (en) * 1979-04-02 1981-10-06 Chimicasa Gmbh Process for the preparation of sweetener containing product
US4252794A (en) * 1979-12-20 1981-02-24 Ici Americas Inc. Gamma-sorbitol polymorph
DE3245170A1 (de) * 1982-12-07 1984-06-07 Merck Patent Gmbh, 6100 Darmstadt Verbesserter sorbit, verfahren zur herstellung und verwendung
DD252003B1 (de) * 1986-08-01 1990-06-20 Hydrierwerk Rodleben Veb Verfahren zur herstellung eines trockensorbitols mit verbesserten anwendungstechnischen eigenschaften
JPH01213245A (ja) * 1988-02-20 1989-08-28 Ueno Seiyaku Oyo Kenkyusho:Kk 固体状ソルビトールの製法
US5158789A (en) * 1991-08-09 1992-10-27 Ici Americas Inc. Melt cocrystallized sorbitol/xylitol compositions
US5139795A (en) * 1991-08-09 1992-08-18 Ici Americas Inc. Melt crystallized xylitol

Also Published As

Publication number Publication date
KR100584828B1 (ko) 2006-05-30
CN1087727C (zh) 2002-07-17
PT915817E (pt) 2001-10-31
JP2001505186A (ja) 2001-04-17
ATE202068T1 (de) 2001-06-15
DE19629640C1 (de) 1997-08-28
ES2159872T3 (es) 2001-10-16
US6150570A (en) 2000-11-21
DE59703810D1 (de) 2001-07-19
KR20000069217A (ko) 2000-11-25
EP0915817A1 (de) 1999-05-19
TW474942B (en) 2002-02-01
WO1998003457A1 (de) 1998-01-29
CN1228756A (zh) 1999-09-15
GR3036335T3 (en) 2001-11-30
IN182140B (pt) 1999-01-09
DK0915817T3 (da) 2001-09-10

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